Metabolism of ibuprofen in higher plants: A model Arabidopsis thaliana cell suspension culture system

Maršík, Petr; Šíša, Miroslav; Lacina, Ondřej; Moťková, Kateřina; Langhansová, Lenka; Rezek, Jan; Vaněk, Tomáš

doi:10.1016/j.envpol.2016.09.074

Cited by 40 publications

(18 citation statements)

References 29 publications

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“…To evaluate the physiological response of plants to xenobiotics and in consideration of lower cost and more controlled conditions, in vitro systems such as cell cultures are often preferred to fields trials and greenhouse experiments, despite their obvious distance from natural conditions [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

Plant organ cultures as masked mycotoxin biofactories: Deciphering the fate of zearalenone in micropropagated durum wheat roots and leaves

et al. 2017

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“Masked mycotoxins” senso strictu are conjugates of mycotoxins resulting from metabolic pathways activated by the interplay between pathogenic fungi and infected plants. Zearalenone, an estrogenic mycotoxin produced by Fusarium spp, was the first masked mycotoxin ever described in the literature, but its biotransformation has been studied to a lesser extent if compared to other compounds such as deoxynivalenol. We presented herein the first application of organ and tissue culture techniques to study the metabolic fate of zearalenone in durum wheat, using an untargeted HR-LCMS approach. A complete, quick absorption of zearalenone by uninfected plant organs was noticed, and its biotransformation into a large spectrum of phase I and phase II metabolites has been depicted. Therefore, wheat organ tissue cultures can be effectively used as a biocatalytic tool for the production of masked mycotoxins, as well as a replicable model for the investigation of the interplay between mycotoxins and wheat physiology.

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Section: Introductionmentioning

confidence: 99%

Plant organ cultures as masked mycotoxin biofactories: Deciphering the fate of zearalenone in micropropagated durum wheat roots and leaves

et al. 2017

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“…For instance, two studies showed that sulfamethoxazole in Arabidopsis thaliana, alongside glycosylation as the main transformation pathway, underwent conjugation with glutathione and leucine after phase I transformation [15] and direct conjugation with pterin and methylsalicylate [17], which were not observed in this study. Neither it was found a conjugation with amino acids, as one of the metabolization pathways of ibuprofen in Arabidopsis thaliana [52]. Notwithstanding the variety of aforementioned identified possible compounds that can play a role during the phase II transformations, novel biotransformation pathways are suggested.…”

Section: Biotransformation Reactionsmentioning

confidence: 96%

“…As with TMP321, methylation has been reported for clindamycin in lettuce [16]. In recent years, several studies have been published dealing with the plant conjugates of various xenobiotics, which could shed light on the fate of ABs in plants including conjugation with sugars, amino acids, a malonyl group, glutathione, glucuronic acid, sulfate, pterin, and methyl salicylate [15,17,30,[52][53][54]. For instance, two studies showed that sulfamethoxazole in Arabidopsis thaliana, alongside glycosylation as the main transformation pathway, underwent conjugation with glutathione and leucine after phase I transformation [15] and direct conjugation with pterin and methylsalicylate [17], which were not observed in this study.…”

Section: Biotransformation Reactionsmentioning

confidence: 99%

Systematic identification of trimethoprim metabolites in lettuce

et al. 2022

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Antibiotics are some of the most widely used drugs. Their release in the environment is of great concern since their consumption is a major factor for antibiotic resistance, one of the most important threats to human health. Their occurrence and fate in agricultural systems have been extensively investigated in recent years. Yet whilst their biotic and abiotic degradation pathways have been thoroughly researched, their biotransformation pathways in plants are less understood, such as in case of trimethoprim. Although trimethoprim has been reported in the environment, its fate in higher plants still remains unknown. A bench-scale experiment was performed and 30 trimethoprim metabolites were identified in lettuce (Lactuca sativa L.), of which 5 belong to phase I and 25 to phase II. Data mining yielded a list of 1018 ions as possible metabolite candidates, which was filtered to a final list of 87 candidates. Molecular structures were assigned for 19 compounds, including 14 TMP metabolites reported for the first time. Alongside well-known biotransformation pathways in plants, additional novel pathways were suggested, namely, conjugation with sesquiterpene lactones, and abscisic acid as a part of phase II of plant metabolism. The results obtained offer insight into the variety of phase II conjugates and may serve as a guideline for studying the metabolization of other chemicals that share a similar molecular structure or functional groups with trimethoprim. Finally, the toxicity and potential contribution of the identified metabolites to the selective pressure on antibiotic resistance genes and bacterial communities via residual antimicrobial activity were evaluated.

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“…Previous research on xenobiotics such as herbicides shows that differences in GSH availability and in the portfolio of GST isoenzymes are associated with xenobiotic resistance (Coleman et al, 1997). Conjugation with various biomolecules was observed in plant metabolism of different PPCPs, including diclofenac (Huber et al, 2012;Fu et al, 2017a), ibuprofen (Marsik et al, 2017), triclosan (Macherius et al, 2012), benzotriazole (Lefevre et al, 2015) and acetaminophen (Bartha et al, 2010;Huber et al, 2009). However, GST-mediated conjugation may play a predominant role, but has been relatively understudied so far (Bartha et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Acetaminophen detoxification in cucumber plants via induction of glutathione S-transferases

Sun

Dudley

McGinnis

et al. 2019

Science of The Total Environment

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Many pharmaceutical and personal care products (PPCPs) enter agroecosystems during reuse of treated wastewater and biosolids, presenting potential impacts on plant development. Here, acetaminophen, one of the most-used pharmaceuticals, was used to explore roles of glutathione (GSH) conjugation in its biotransformation in crop plants. Acetaminophen was taken up by plants, and conjugated quickly with GSH. After exposure to 5 mg L acetaminophen for 144 h, GSH-acetaminophen conjugates were 15.2 ± 1.3 nmol g and 1.2 ± 0.1 nmol g in cucumber roots and leaves, respectively. Glutathione-acetaminophen was also observed in common bean, alfalfa, tomato, and wheat. Inhibition of cytochrome P450 decreased GSH conjugation. Moreover, the GSH conjugate was found to further convert to cysteine and N-acetylcysteine conjugates. Glutathione S-transferase activity was significantly elevated after exposure to acetaminophen, while levels of GSH decreased by 55.4% in roots after 48 h, followed by a gradual recovery thereafter. Enzymes involved in GSH synthesis, regeneration and transport were consistently induced to maintain the GSH homeostasis. Therefore, GST-mediated conjugation likely played a crucial role in minimizing phytotoxicity of acetaminophen and other PPCPs in plants.

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Metabolism of ibuprofen in higher plants: A model Arabidopsis thaliana cell suspension culture system

Cited by 40 publications

References 29 publications

Plant organ cultures as masked mycotoxin biofactories: Deciphering the fate of zearalenone in micropropagated durum wheat roots and leaves

Plant organ cultures as masked mycotoxin biofactories: Deciphering the fate of zearalenone in micropropagated durum wheat roots and leaves

Systematic identification of trimethoprim metabolites in lettuce

Acetaminophen detoxification in cucumber plants via induction of glutathione S-transferases

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